US6258367B1 - Cosmetic composition comprising at least one nonionic amphiphilic associative polyurethane and at least one quaternary silicone - Google Patents

Cosmetic composition comprising at least one nonionic amphiphilic associative polyurethane and at least one quaternary silicone Download PDF

Info

Publication number
US6258367B1
US6258367B1 US09/402,797 US40279799A US6258367B1 US 6258367 B1 US6258367 B1 US 6258367B1 US 40279799 A US40279799 A US 40279799A US 6258367 B1 US6258367 B1 US 6258367B1
Authority
US
United States
Prior art keywords
composition according
ranges
radicals
quaternary ammonium
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
US09/402,797
Inventor
Christine Dupuis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Assigned to L'OREAL S.A. reassignment L'OREAL S.A. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DUPUIS, CHRISTINE
Application granted granted Critical
Publication of US6258367B1 publication Critical patent/US6258367B1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers

Definitions

  • the present invention relates to cosmetic compositions containing a novel thickening system based on associative polyurethanes, as well as to their use in particular as leave-in haircare gels or styling gels.
  • the thickening and/or gelation of aqueous media with polymers has been an important subject of cosmetic research for a long time.
  • the production of an advantageous thickening effect with a water-soluble polymer generally assumes a high molar mass and a large hydrodynamic volume.
  • the gelation of an aqueous medium is then considered as being the result of a three-dimensional polymer network obtained by crosslinking linear polymers or by copolymerizing bifunctional and polyfunctional monomers.
  • the use of such polymers of very high molar mass poses a certain number of problems, such as the relatively unpleasant texture and the difficulty in spreading the gels obtained.
  • One advantageous approach consists in using, as thickeners, polymers capable of reversibly self-associating or of associating with other molecules or particles. This physical association gives rise to thixotropic or rheofluidizing macromolecular systems, i.e. systems whose viscosity depends on the shear forces to which they are subjected.
  • Such polymers capable of reversibly self-associating or of associating with other molecules are known as “associative polymers”.
  • the forces of interaction in play can be very different in nature, for example of electrostatic nature, of hydrogen bonding type or hydrophobic interactions.
  • amphiphilic polymers i.e. polymers comprising one or more hydrophilic portions which make them soluble in water, and one or more hydrophobic zones via which the polymers interact and self-asserble or assemble with other molecules.
  • compositions based on associative polymers and surfactants do not always have the desired cosmetic properties.
  • the presence of surfactants can bring about an undesirable change in the cosmetic properties of the said compositions, such as the properties of application or of feel after drying.
  • French patent application No. 2,738,835 relates to aqueous cosmetic compositions thickened using at least one amphiphilic polymer associated with at least one protein containing a hydrophobic group.
  • the gel obtained by this combination has a very melting texture and is pleasant to apply.
  • the final feel on dried hair is more pleasant and less laden.
  • the gel moreover has excellent styling power.
  • One subject of the present invention is thus a cosmetic composition
  • a cosmetic composition comprising at least one associative nonionic polyurethane in combination with at least one silicone containing quaternary ammonium groups.
  • Another subject of the present invention is the use of the combination of at least associative nonionic polyurethane and at least one silicone containing quaternary ammonium groups as a thickening system, in particular for the manufacture of leave-in haircare and styling gels.
  • a third subject of the invention is a cosmetic process for treating the hair with cosmetic compositions comprising at least one nonionic associative polyurethane and at least one silicone containing quaternary ammonium groups.
  • compositions in accordance with the invention are essentially characterized in that they contain, in a cosmetically acceptable medium,
  • nonionic associative polyurethanes used in the present invention preferably correspond to the general formula
  • At least one of the radicals R 1 and R 2 represents a C 8 -C 18 higher alkyl group and the other, where appropriate, represents a C 1 -C 6 lower alkyl group, preferably a C 1 -C 4 lower alkyl group,
  • R 3 represents a C 4 -C 36 , preferably C 6 -C 10 , hydrocarbon-based radical,
  • R 4 represents a hydrogen atom or a C 1 -C 6 alkyl radical, preferably a hydrogen atom,
  • b is from 1 to 4.
  • C 1 -C 5 lower alkyl group means an alkyl group containing a linear or branched chain comprising from 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, n-butyl, n-pentyl and n-hexyl radicals, as well as the corresponding branched isomers.
  • the C 8 -C 18 higher alkyl groups denote alkyl groups containing a linear or branched chain comprising from 8 to 18 carbon atoms, such as octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl radicals.
  • only one of the radicals R 1 and R 2 represents a C 8 -C 18 higher alkyl chain and the other represents a C 1 -C 6 lower alkyl group.
  • An associative polyurethane in which one of the radicals in ⁇ , ⁇ represents an octadecyl group and the other represents a methyl group is used in particular.
  • the associative polyurethanes used in the compositions of the present invention are used in the form of an aqueous solution or suspension optionally containing a certain amount of soluble starch.
  • This starch can be any starch extracted from natural sources, such as wheat starch, cornstarch, rice starch, potato starch, etc. and which has been chemically, enzymatically or microbiologically modified so as to be soluble in water.
  • a preferred polymer is sold by the company Rohm & Haas under the name Acrysol 46. It is a polyurethane obtained by condensation of hexamethylene diisocyanate and polyethylene glycol, and bearing, on average, a methyl residue and an octadecyl residue at its ends, respectively. This polymer is in the form of an aqueous solution containing 15% by weight of polyurethane active material also containing 3-5% of an enzymatically modified starch matrix.
  • silicone containing quaternary ammonium groups means any silicone comprising one or more quaternary ammonium groups. These quaternary ammonium groups can be attached in the ⁇ - ⁇ positions or in the form of side groups. They can be attached directly to the polysiloxane skeleton or can be borne by hydrocarbon-based chains, in particular polyoxyalkylene chains.
  • silicone means any polymer having a structure based on the alternation of silicon and oxygen atoms, linked together via so-called siloxane (—Si—O—Si—) bonds, and also characterized by the existence of silicon-carbon bonds.
  • These silicones, or polysiloxanes are generally obtained by polycondensation of suitably functionalized silanes.
  • the hydrocarbon-based radicals most commonly borne by the silicon atoms are lower alkyl radicals, in particular methyl, fluoroalkyl radicals, aryl radicals and in particular phenyl.
  • silicones containing quaternary ammonium groups of the present invention are chosen, for example, from the compounds corresponding to the following general formulae:
  • radicals R 5 which may be identical or different, represent linear or branched C 1 -C 30 alkyl radicals, or phenyl radicals;
  • radicals R 6 which may be identical or different, represent a group —C e H 2e —O—(C 2 H 4 O) c —(C 3 H 6 O) d —R 8 or —C e H 2e —O—(C 4 H 8 O) c —R 8 ,
  • radicals R 7 which may be identical or different, denote a linear or branched C 1 -C 12 alkyl radical and preferably a methyl radical;
  • radicals R 8 which may be identical or different, represent a group
  • radicals R 11 represent, independently, a linear or branched C 1 -C 22 alkyl or C 2 -C 22 alkenyl radical, optionally bearing one or more OH groups, or represent a group C h H 2h Z j COR 12 ;
  • R 9 , R 10 and R 12 which may be identical or different, represent linear or branched C 1 -C 22 alkyl or C 2 -C 22 alkenyl radicals, optionally bearing one or more OH groups, or R 10 can form, with a portion of R 11 , an imidazoline ring,
  • c ranges from 0 to 50
  • d ranges from 0 to 50
  • e and f range, independently, from 0 to 4,
  • n ranges from 0 to 20
  • n ranges from 0 to 500
  • o ranges from 0 to 20
  • p ranges from 1 to 50
  • x ranges from 1 to 100
  • g ranges from 0 to 2
  • h ranges from 1 to 4,
  • Z represents an oxygen or nitrogen atom
  • i 0 or 1
  • a ⁇ represents a halide ion or an organic anion of carboxylate, phosphate, alkanesulphate or sulphate type.
  • Such silicones are sold, for example, by the company Goldschmidt under the names Abil Quat 3272, Abil B 9905, Abil Quat 3474 and Abil K 3270, by the company Lipo France under the names Silquat Q-100, Biosil Basics Cetylsil, Silquat Q-200 WS, Silquat AX, Silquat AC, Silquat AD and Silquat AM, all manufactured by the company Siltech, by the company OSI under the name Magnasoft Exhaust and Silsoft C-880, and by the company UCIB under the names Pecosil 14-PQ and Pecosil 36-PQ (manufactured by Phoenix Chemical).
  • Silicones containing quaternary ammonium groups which are used in accordance with the invention can be in the form of aqueous solutions or optionally in the form of dispersions or emulsions in water.
  • the silicones containing quaternary ammonium groups and the associative polyurethanes are used in amounts which are sufficient to obtain a satisfactory thickening or gelation of the aqueous medium.
  • an amount of associative polyurethanes of between 0.1 and 10% by weight, and preferably between 0.5 and 5% by weight, in terms of active material relative to the total weight of the composition, is used in particular.
  • the silicone(s) containing quaternary ammonium groups is (are) present in a proportion of from 0.01 to 10% by weight, preferably in a proportion of from 0.1 to 5% by weight, of active material relative to the total weight of the composition.
  • the silicones are preferably used in an amount such that the silicone/amphiphilic polyurethane weight ratio is between 0.1 and 10.
  • the cosmetically acceptable medium preferably consists of water and can also contain cosmetically acceptable solvents, for example lower monoalcohols such as ethanol or isopropanol, glycols such as ethylene glycol, glycol ethers such as the alkyl ethers of ethylene glycol or of diethylene glycol, or alternatively fatty acid esters, all of these solvents being used alone or in the form of a mixture.
  • cosmetically acceptable solvents for example lower monoalcohols such as ethanol or isopropanol, glycols such as ethylene glycol, glycol ethers such as the alkyl ethers of ethylene glycol or of diethylene glycol, or alternatively fatty acid esters, all of these solvents being used alone or in the form of a mixture.
  • the haircare or styling gels can also contain one or more additives usually used in such hair compositions. Mention may be made, for example, of fragrances, dyes, preserving agents, sunscreens, vitamins, pH regulators, etc. It is clearly understood that the choice of these compounds should take into account possible interactions with the thickening system. A person skilled in the art will take care to ensure that the addition of these additives will not have an unfavourable influence on the advantageous properties of the compositions obtained by means of the present invention.
  • One preferred cosmetic process for treating the hair consists in applying and homogeneously distributing the compositions defined above on the hair and in drying the hair thus treated without rinsing it.
  • aqueous compositions below are prepared, comprising 2% by weight of associatve polyurethane active material and 1% of silicone active material containing quaternary ammonium groups or of cationic silicones.
  • composition polyurethane silicone silicone silicone obtained Acrysol 46 Abil Quat 3272 quaternized gel Acrysol 46 Silquat Q-100 quaternized gel Acrysol 46 Biosil Basic quaternized gel Cetylsil Acrysol 46 SLM 23056/1 non- fluid quaternized solution Acrysol 46 Finish CT 110E non- fluid quaternized solution Acrysol 46 none — fluid solution
  • the silicones used are as follows:
  • Abil Quat 3272 is a polydimethylsiloxane containing quaternary ammonium acetate groups containing ⁇ and ⁇ coconut fatty chains (50% solution in propylene glycol) sold by the company Goldschmidt;
  • Silquat Q-100 is a polydimethylsiloxane containing propyloxy-hydroxy-2-propyltrimethylammonium chloride groups (alcoholic 70% solution) sold by the company Lipo France;
  • Biosil Basic Cetylsil is an oxyethylenated polydimethylsiloxane containing phthalic ester/cetyltriethylammonium chloride groups (aqueous 40% solution) sold by the company Siltech;
  • Finish CT110 E is a polydimethyl/methylcyclohexylaminopropyl siloxane (as a nonionic amulsion) sold by the company Wacker;
  • SLM 23 056/1 is a polydimethylsiloxane containing aminoethylaminopropyl and ⁇ , ⁇ lauryl groups, sold by the company Wacker.
  • a care gel having the composition below was prepared:
  • fragrance dye, preserving agent demineralized water q.s. 100 g
  • a care gel having the composition below was prepared:
  • fragrance dye, preserving agent demineralized water q.s. 100 g

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

A cosmetic composition having, in a cosmetically acceptable medium, at least one nonionic amphiphilic associative polyurethane, and at least one silicone containing quaternary ammonium groups.

Description

This application is a 371 of PCT/FR98/02865 filed Dec. 23, 1998.
The present invention relates to cosmetic compositions containing a novel thickening system based on associative polyurethanes, as well as to their use in particular as leave-in haircare gels or styling gels.
The thickening and/or gelation of aqueous media with polymers has been an important subject of cosmetic research for a long time. The production of an advantageous thickening effect with a water-soluble polymer generally assumes a high molar mass and a large hydrodynamic volume. The gelation of an aqueous medium is then considered as being the result of a three-dimensional polymer network obtained by crosslinking linear polymers or by copolymerizing bifunctional and polyfunctional monomers. However, the use of such polymers of very high molar mass poses a certain number of problems, such as the relatively unpleasant texture and the difficulty in spreading the gels obtained.
One advantageous approach consists in using, as thickeners, polymers capable of reversibly self-associating or of associating with other molecules or particles. This physical association gives rise to thixotropic or rheofluidizing macromolecular systems, i.e. systems whose viscosity depends on the shear forces to which they are subjected.
Such polymers capable of reversibly self-associating or of associating with other molecules are known as “associative polymers”. The forces of interaction in play can be very different in nature, for example of electrostatic nature, of hydrogen bonding type or hydrophobic interactions.
One specific case of associative polymers is amphiphilic polymers, i.e. polymers comprising one or more hydrophilic portions which make them soluble in water, and one or more hydrophobic zones via which the polymers interact and self-asserble or assemble with other molecules.
It is known practice to prepare hair compositions in gel form using, as thickening system, such associative amphiphilic polymers, in combination with surfactants. It is thought that the advantageous rheological properties of the gels thus obtained result from the formation of mixed micelles formed by the surfactants and by the hydrophobic portions of the amphiphilic polymers, these micelles constituting a multitude of physical crosslinking points.
However, these compositions based on associative polymers and surfactants do not always have the desired cosmetic properties. Thus, the presence of surfactants, even in small amounts, can bring about an undesirable change in the cosmetic properties of the said compositions, such as the properties of application or of feel after drying. Moreover, in particular in the sector of leave-in haircare or styling gels, it is important to be able to distribute the product uniformly over the entire head of hair so as to avoid excessive loads and the cosmetic defects resulting therefrom.
French patent application No. 2,738,835 relates to aqueous cosmetic compositions thickened using at least one amphiphilic polymer associated with at least one protein containing a hydrophobic group.
It has now been discovered that it is possible to obtain a good thickening, or even gelling, effect and advantageous cosmetic properties by combining associative amphiphilic polyurethanes with silicones containing quaternary ammonium groups.
The gel obtained by this combination has a very melting texture and is pleasant to apply. The final feel on dried hair is more pleasant and less laden. The gel moreover has excellent styling power.
One subject of the present invention is thus a cosmetic composition comprising at least one associative nonionic polyurethane in combination with at least one silicone containing quaternary ammonium groups.
Another subject of the present invention is the use of the combination of at least associative nonionic polyurethane and at least one silicone containing quaternary ammonium groups as a thickening system, in particular for the manufacture of leave-in haircare and styling gels.
A third subject of the invention is a cosmetic process for treating the hair with cosmetic compositions comprising at least one nonionic associative polyurethane and at least one silicone containing quaternary ammonium groups.
Other subjects will become apparent on reading the description and the examples which follow.
The cosmetic compositions in accordance with the invention are essentially characterized in that they contain, in a cosmetically acceptable medium,
(A) at least one amphiphilic nonionic associative polyurethane, and
(B) at least one silicone containing quaternary ammonium groups.
The nonionic associative polyurethanes used in the present invention preferably correspond to the general formula
Figure US06258367-20010710-C00001
in which
at least one of the radicals R1 and R2 represents a C8-C18 higher alkyl group and the other, where appropriate, represents a C1-C6 lower alkyl group, preferably a C1-C4 lower alkyl group,
R3 represents a C4-C36, preferably C6-C10, hydrocarbon-based radical,
R4 represents a hydrogen atom or a C1-C6 alkyl radical, preferably a hydrogen atom,
a ranges, independently, from 90 to 600, and
b is from 1 to 4.
According to the invention, the expression “C1-C5 lower alkyl group” means an alkyl group containing a linear or branched chain comprising from 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, n-butyl, n-pentyl and n-hexyl radicals, as well as the corresponding branched isomers.
In accordance with the invention, the C8-C18 higher alkyl groups denote alkyl groups containing a linear or branched chain comprising from 8 to 18 carbon atoms, such as octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl radicals.
In one preferred embodiment, only one of the radicals R1 and R2 represents a C8-C18 higher alkyl chain and the other represents a C1-C6 lower alkyl group.
An associative polyurethane in which one of the radicals in α, ω represents an octadecyl group and the other represents a methyl group is used in particular.
The associative polyurethanes used in the compositions of the present invention are used in the form of an aqueous solution or suspension optionally containing a certain amount of soluble starch. This starch can be any starch extracted from natural sources, such as wheat starch, cornstarch, rice starch, potato starch, etc. and which has been chemically, enzymatically or microbiologically modified so as to be soluble in water.
A preferred polymer is sold by the company Rohm & Haas under the name Acrysol 46. It is a polyurethane obtained by condensation of hexamethylene diisocyanate and polyethylene glycol, and bearing, on average, a methyl residue and an octadecyl residue at its ends, respectively. This polymer is in the form of an aqueous solution containing 15% by weight of polyurethane active material also containing 3-5% of an enzymatically modified starch matrix.
In accordance with the invention, the expression “silicone containing quaternary ammonium groups” means any silicone comprising one or more quaternary ammonium groups. These quaternary ammonium groups can be attached in the α-ω positions or in the form of side groups. They can be attached directly to the polysiloxane skeleton or can be borne by hydrocarbon-based chains, in particular polyoxyalkylene chains.
According to the invention, in accordance with the generally accepted meaning, the term “silicone” means any polymer having a structure based on the alternation of silicon and oxygen atoms, linked together via so-called siloxane (—Si—O—Si—) bonds, and also characterized by the existence of silicon-carbon bonds. These silicones, or polysiloxanes, are generally obtained by polycondensation of suitably functionalized silanes. The hydrocarbon-based radicals most commonly borne by the silicon atoms are lower alkyl radicals, in particular methyl, fluoroalkyl radicals, aryl radicals and in particular phenyl.
The silicones containing quaternary ammonium groups of the present invention are chosen, for example, from the compounds corresponding to the following general formulae:
Figure US06258367-20010710-C00002
in which formulae:
the radicals R5, which may be identical or different, represent linear or branched C1-C30 alkyl radicals, or phenyl radicals;
the radicals R6, which may be identical or different, represent a group —CeH2e—O—(C2H4O)c—(C3H6O)d—R8 or —CeH2e—O—(C4H8O)c—R8,
the radicals R7, which may be identical or different, denote a linear or branched C1-C12 alkyl radical and preferably a methyl radical;
the radicals R8, which may be identical or different, represent a group
Figure US06258367-20010710-C00003
the radicals R11 represent, independently, a linear or branched C1-C22 alkyl or C2-C22 alkenyl radical, optionally bearing one or more OH groups, or represent a group ChH2hZjCOR12;
R9, R10 and R12, which may be identical or different, represent linear or branched C1-C22 alkyl or C2-C22 alkenyl radicals, optionally bearing one or more OH groups, or R10 can form, with a portion of R11, an imidazoline ring,
c ranges from 0 to 50,
d ranges from 0 to 50,
e and f range, independently, from 0 to 4,
m ranges from 0 to 20,
n ranges from 0 to 500,
o ranges from 0 to 20,
p ranges from 1 to 50,
x ranges from 1 to 100,
g ranges from 0 to 2,
h ranges from 1 to 4,
Z represents an oxygen or nitrogen atom,
i is 0 or 1, and
A− represents a halide ion or an organic anion of carboxylate, phosphate, alkanesulphate or sulphate type.
Such silicones are sold, for example, by the company Goldschmidt under the names Abil Quat 3272, Abil B 9905, Abil Quat 3474 and Abil K 3270, by the company Lipo France under the names Silquat Q-100, Biosil Basics Cetylsil, Silquat Q-200 WS, Silquat AX, Silquat AC, Silquat AD and Silquat AM, all manufactured by the company Siltech, by the company OSI under the name Magnasoft Exhaust and Silsoft C-880, and by the company UCIB under the names Pecosil 14-PQ and Pecosil 36-PQ (manufactured by Phoenix Chemical).
These silicones are described in particular in patents EP 530,974, DE 3,719,086, DE 3,705,121, EP 617,607 and EP 714,654.
Silicones containing quaternary ammonium groups which are used in accordance with the invention can be in the form of aqueous solutions or optionally in the form of dispersions or emulsions in water.
The silicones containing quaternary ammonium groups and the associative polyurethanes are used in amounts which are sufficient to obtain a satisfactory thickening or gelation of the aqueous medium.
An amount of associative polyurethanes of between 0.1 and 10% by weight, and preferably between 0.5 and 5% by weight, in terms of active material relative to the total weight of the composition, is used in particular.
In the compositions of the present invention, the silicone(s) containing quaternary ammonium groups is (are) present in a proportion of from 0.01 to 10% by weight, preferably in a proportion of from 0.1 to 5% by weight, of active material relative to the total weight of the composition.
The silicones are preferably used in an amount such that the silicone/amphiphilic polyurethane weight ratio is between 0.1 and 10.
The cosmetically acceptable medium preferably consists of water and can also contain cosmetically acceptable solvents, for example lower monoalcohols such as ethanol or isopropanol, glycols such as ethylene glycol, glycol ethers such as the alkyl ethers of ethylene glycol or of diethylene glycol, or alternatively fatty acid esters, all of these solvents being used alone or in the form of a mixture.
The haircare or styling gels can also contain one or more additives usually used in such hair compositions. Mention may be made, for example, of fragrances, dyes, preserving agents, sunscreens, vitamins, pH regulators, etc. It is clearly understood that the choice of these compounds should take into account possible interactions with the thickening system. A person skilled in the art will take care to ensure that the addition of these additives will not have an unfavourable influence on the advantageous properties of the compositions obtained by means of the present invention.
One preferred cosmetic process for treating the hair, according to the invention, consists in applying and homogeneously distributing the compositions defined above on the hair and in drying the hair thus treated without rinsing it.
It is clearly understood that the description hereinabove has been given purely for illustrative purposes and without any limitation being implied, and that variations or modifications may be made thereto in the context of the present invention.
The examples which follow are intended to illustrate the invention without thereby being limiting in nature.
EXAMPLE 1
The aqueous compositions below are prepared, comprising 2% by weight of associatve polyurethane active material and 1% of silicone active material containing quaternary ammonium groups or of cationic silicones.
consistency
of the
Associative nature of the composition
polyurethane silicone silicone obtained
Acrysol 46 Abil Quat 3272 quaternized gel
Acrysol 46 Silquat Q-100 quaternized gel
Acrysol 46 Biosil Basic quaternized gel
Cetylsil
Acrysol 46 SLM 23056/1 non- fluid
quaternized solution
Acrysol 46 Finish CT 110E non- fluid
quaternized solution
Acrysol 46 none — fluid
solution
The silicones used are as follows:
Abil Quat 3272 is a polydimethylsiloxane containing quaternary ammonium acetate groups containing α and ω coconut fatty chains (50% solution in propylene glycol) sold by the company Goldschmidt;
Silquat Q-100 is a polydimethylsiloxane containing propyloxy-hydroxy-2-propyltrimethylammonium chloride groups (alcoholic 70% solution) sold by the company Lipo France;
Biosil Basic Cetylsil is an oxyethylenated polydimethylsiloxane containing phthalic ester/cetyltriethylammonium chloride groups (aqueous 40% solution) sold by the company Siltech;
Finish CT110 E is a polydimethyl/methylcyclohexylaminopropyl siloxane (as a nonionic amulsion) sold by the company Wacker; and
SLM 23 056/1 is a polydimethylsiloxane containing aminoethylaminopropyl and α, ω lauryl groups, sold by the company Wacker.
It is found that the combination of preferred amphiphilic polyurethane of the present invention (Acrysol 46) and of a non-quaternized silicone does not allow gelation of the aqueous medium, but instead gives rise to a fluid solution whose viscosity is little different from that of a polyurethane solution alone. On the other hand, the addition of only 1% by weight of one of the silicones containing quaternary ammonium groups of the present invention to a polyurethane solution is reflected by satisfactory gelation of this same aqueous medium.
EXAMPLE 2
A care gel having the composition below was prepared:
Acrysal 46 2.5% active material
Abil Quat 3272 1.5% active material
fragrance, dye, preserving agent demineralized water q.s. 100 g
EXAMPLE 3
A care gel having the composition below was prepared:
Acrysol 46 3% active material
Sil Quat Q100 2% active material
fragrance, dye, preserving agent demineralized water q.s. 100 g

Claims (21)

What is claimed is:
1. A cosmetic composition comprising, in a cosmetically acceptable medium,
(A) at least one nonionic amphiphilic associative polyurethane, and
(B) at least one silicone containing quaternary ammonium groups.
2. A cosmetic composition according to claim 1, wherein the at least one nonionic amphiphilic associative polyurethane has the formula (I):
Figure US06258367-20010710-C00004
in which
at least one of the radicals R1 and R2 is a higher alkyl group having 8 to 18 carbons,
R3 is a hydrocarbon-based radical having from 4 to 36 carbons,
R4 is chosen from a hydrogen atom and C1-C6 alkyl radicals,
a ranges, independently, from 90 to 600, and
b ranges from 1 to 4.
3. The composition according to claim 2, wherein R3 has from 6 to 10 carbons.
4. The composition according to claim 2, wherein R4 is a hydrogen atom.
5. The composition according to claim 2, wherein one of the groups R1 and R2 is a C8-C18 higher alkyl group and the other group is a C1-C6 lower alkyl group.
6. The composition according to claim 5, wherein the lower alkyl group has 1 to 4 carbons.
7. The composition according to claim 6, wherein the higher alkyl group is an octadecyl group and the lower alkyl group is a methyl group.
8. The composition according to claim 7, wherein the at least one nonionic amphiphilic associative polyurethane of formula (I) is obtained by polycondensation of hexamethylene diisocyanate and polyethylene glycol.
9. The composition according to claim 2, wherein the at least one nonionic amphiphilic associative polyurethane of formula (I) is in a solution or suspension in water, which also contains chemically, enzymatically or microbiologically modified soluble starch.
10. The composition according to claim 1, wherein the at least one silicone containing quaternary ammonium groups is chosen from a silicone corresponding to one of the following formulae:
Figure US06258367-20010710-C00005
in which formulae:
the R5 radicals, which may be identical or different, are chosen from or phenyl radicals and linear and branched C1-C30 alkyl radicals;
the R6 radicals, which may be identical or different, are chosen from —CeH2e—O—(C2H4O)c—(C3H6O)d—R8 and —CeH2e—O—(C4H8O)c—R8,
the R7 radical is chosen from linear and branched C1-C12 alkyl radicals;
the R8 radicals, which may be identical or different, are a
Figure US06258367-20010710-C00006
the R11 radicals are, independently, chosen from a ChH2hZjCOR12 group, and linear or branched C1-C22 alkyl and C2-C22 alkenyl radicals, optionally bearing one or more OH groups,
the R9, R10 and R12 radicals, which may be identical or different, are chosen from linear and branched C1-C22 alkyl and C2-C22 alkenyl radicals, optionally bearing one or more OH groups, or R10 can form, with a portion of R11, an imidazoline ring,
c ranges from 0 to 50,
d ranges from 0 to 50,
e and f range, independently, from 0 to 4,
m ranges from 0 to 20,
n ranges from 0 to 500,
o ranges from 0 to 20,
p ranges from 1 to 50,
x ranges from 1 to 100,
g ranges from 0 to 2,
h ranges from 1 to 4,
Z is chosen from oxygen and nitrogen,
i is 0 or 1, and
A− is chosen from halide ions and organic carboxylate, phosphate, alkanesulphate, and sulphate anions.
11. The composition according to claim 10, wherein R7 radical is a methyl radical.
12. The composition according to claim 1, wherein the at least one silicone containing quaternary ammonium groups is in a solution, suspension or dispersion in water.
13. The composition according to claim 10, wherein the at least one silicone containing quaternary ammonium groups is chosen from polydimethylsiloxanes containing quaternary ammonium acetate groups containing α and ω coconut fatty chains, polydimethylsiloxanes containing propyloxy-hydroxy-2-propyltrimethylammonuium chloride groups, and oxyethylenated polydimethylsiloxanes containing phthalic ester/cetyltriethylammonium chloride groups.
14. The composition according to claim 1, wherein the at least one nonionic amphiphilic associative polyurethane of formula (I) is present in an amount of from 0.1 to 10% by weight of active material relative to the total weight of the composition.
15. The composition according to claim 14, wherein the at least one nonionic amphiphilic associative polyurethane of formula (I) is present in an amount of from 0.5 to 5% by weight of active material relative to the total weight of the composition.
16. The composition according to claim 1, wherein the at least one silicone containing quaternary ammonium groups is present in an amount of from 0.01 to 10% by weight of active material relative to the total weight of the composition.
17. The composition according to claim 16, wherein the at least one silicone containing quaternary ammonium groups is present in an amount of from 0.1 to 5% by weight of active material relative to the total weight of the composition.
18. The composition according to claim 1, wherein the weight ratio of the at least one silicone containing quaternary ammonium groups and the at least one nonionic amphiphilic polyurethane ranges from about 0.1 to 10.
19. A leave-in haircare gel or styling gel comprising, in a cosmetically acceptable medium:
(A) at least one nonionic amphiphilic associative polyurethane, and
(B) at least one silicone containing quaternary ammonium groups.
20. A process of thickening a cosmetic composition comprising adding at least one nonionic amphiphilic associative polyurethane and at least one silicone containing quaternary ammonium groups to the composition in an amount effective to thicken said composition.
21. A process for treating hair comprising applying a composition comprising, in a cosmetically acceptable medium:
(A) at least one nonionic associative polyurethane, and
(B) at least one silicone containing quaternary ammonium groups to the hair and drying the hair without rinsing said composition from the hair.
US09/402,797 1998-02-13 1998-12-23 Cosmetic composition comprising at least one nonionic amphiphilic associative polyurethane and at least one quaternary silicone Expired - Fee Related US6258367B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9801776 1998-02-13
FR9801776A FR2774902B1 (en) 1998-02-13 1998-02-13 COSMETIC COMPOSITION BASED ON ASSOCIATIVE POLYURETHANS AND QUATERNARY SILICONES
PCT/FR1998/002865 WO1999040892A1 (en) 1998-02-13 1998-12-23 Cosmetic composition based on associative polyurethanes and quaternary silicones

Publications (1)

Publication Number Publication Date
US6258367B1 true US6258367B1 (en) 2001-07-10

Family

ID=9522962

Family Applications (1)

Application Number Title Priority Date Filing Date
US09/402,797 Expired - Fee Related US6258367B1 (en) 1998-02-13 1998-12-23 Cosmetic composition comprising at least one nonionic amphiphilic associative polyurethane and at least one quaternary silicone

Country Status (14)

Country Link
US (1) US6258367B1 (en)
EP (1) EP0975315B1 (en)
JP (1) JP3930060B2 (en)
CN (1) CN1259035A (en)
AT (1) ATE222086T1 (en)
AU (1) AU1882999A (en)
BR (1) BR9807939A (en)
CA (1) CA2285684C (en)
DE (1) DE69807205T2 (en)
DK (1) DK0975315T3 (en)
ES (1) ES2182389T3 (en)
FR (1) FR2774902B1 (en)
PT (1) PT975315E (en)
WO (1) WO1999040892A1 (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030129210A1 (en) * 2002-01-09 2003-07-10 Economy Mud Products Company Uses of flaked cationic potato starch
US20050129639A1 (en) * 2003-11-07 2005-06-16 Eric Quemin Makeup composition comprising an emulsion
US20060184147A1 (en) * 2005-02-16 2006-08-17 Hamed Othman A Treatment composition for making acquisition fluff pulp in sheet form
US20080312397A1 (en) * 2007-06-14 2008-12-18 Bausch & Lomb Incorporated Silicone-Containing Prepolymers
US20100256244A1 (en) * 2009-04-03 2010-10-07 Kroff Chemical Company Demulsification Compositions, Systems and Methods for Demulsifying and Separating Aqueous Emulsions
EP2335680A1 (en) * 2009-12-18 2011-06-22 KPSS-Kao Professional Salon Services GmbH Cleansing composition
US20120168664A1 (en) * 2009-09-15 2012-07-05 Evonik Goldschmidt Gmbh Novel polysiloxanes having quaternary ammonium groups and use thereof

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10002513A1 (en) 2000-01-21 2001-08-16 Wella Ag Composition for a hair treatment composition in the form of an aerosol foam
US6482969B1 (en) * 2001-10-24 2002-11-19 Dow Corning Corporation Silicon based quaternary ammonium functional compositions and methods for making them
JP4993426B2 (en) * 2005-08-19 2012-08-08 株式会社 資生堂 Hair cosmetics
WO2009112417A1 (en) * 2008-03-11 2009-09-17 Momentive Performance Materials Gmbh Novel ammonium polyurethane and/or polycarbonate compounds

Citations (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3705121A1 (en) 1987-02-18 1988-09-01 Goldschmidt Ag Th POLYQUATERIAL POLYSILOXANE POLYMERS, THEIR PRODUCTION AND USE IN COSMETIC PREPARATIONS
EP0339712A1 (en) 1988-04-28 1989-11-02 Berol Nobel AB Method for preparing flat or semi-flat water paints
US4891166A (en) 1987-06-06 1990-01-02 Th. Goldschmidt Ag Diquaternary polysiloxanes, their synthesis and use in cosmetic preparations
EP0412705A2 (en) 1989-08-07 1991-02-13 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions
EP0415705A2 (en) 1989-08-28 1991-03-06 Minnesota Mining And Manufacturing Company Conformable polymeric marking sheet
EP0530974A1 (en) 1991-08-05 1993-03-10 Unilever Plc Hair care composition
US5294692A (en) 1993-06-30 1994-03-15 National Starch And Chemical Investment Holding Corporation Associative monomers and polymers
US5344643A (en) 1990-12-21 1994-09-06 Dowbrands L.P. Shampoo-conditioning composition and method of making
EP0617607A1 (en) 1992-10-20 1994-10-05 Alberto Culver Co Hair care composition containing dispersed silicone oil.
EP0637600A1 (en) 1993-08-04 1995-02-08 L'oreal New polyester polyurethanes, their preparation process, pseudo-latex prepared from these polyester polyurethanes and their use in cosmetic compositions
EP0648485A1 (en) 1993-10-15 1995-04-19 L'oreal Aqueous nail varnish containing dispersed particles of anionic polyester-polyurethane
US5478562A (en) 1992-02-07 1995-12-26 L'oreal Cosmetic composition containing at least one surface-active agent of the alkyl polyglycoside and/or polyglycerolated type and at least one polyetherurethane
DE4438846A1 (en) 1994-11-02 1996-05-09 Henkel Kgaa Hair treatment products
EP0714654A1 (en) 1994-12-03 1996-06-05 Wella Aktiengesellschaft Composition and process for permanent waving of hair
FR2733910A1 (en) 1995-05-12 1996-11-15 Oreal COMPOSITION IN THE FORM OF AEROSOL FOAM BASED ON POLYURETHANE AND ANIONIC POLYMER
FR2738835A1 (en) 1995-09-18 1997-03-21 Oreal THICKNESS COMPOSITION IN AQUEOUS MEDIUM, PROCESS FOR THICKENING OF AN AQUEOUS MEDIUM AND USES IN COSMETICS
US5661118A (en) 1994-04-22 1997-08-26 L'oreal Hair and skin washing and treatment compositions based on ceramide and/or glycoceramide and on polymers containing cationic groups
FR2750047A1 (en) 1996-06-19 1997-12-26 Oreal Cosmetic or dermatological composition in form of viscous aqueous gel for topical application in hair dressing and styling gels
EP0824914A1 (en) 1996-08-16 1998-02-25 National Starch and Chemical Investment Holding Corporation Thickened personal care composition
FR2758262A1 (en) 1997-01-14 1998-07-17 Oreal COSMETIC OR DERMATOLOGICAL COMPOSITION IN THE FORM OF A GEL CONTAINING A MIXTURE OF AN ASSOCIATIVE COPOLYMER, A SURFACTANT AND AN INSOLUBLE PACKAGING AGENT

Patent Citations (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3705121A1 (en) 1987-02-18 1988-09-01 Goldschmidt Ag Th POLYQUATERIAL POLYSILOXANE POLYMERS, THEIR PRODUCTION AND USE IN COSMETIC PREPARATIONS
EP0282720A2 (en) 1987-02-18 1988-09-21 Th. Goldschmidt AG Polyquaternary polysiloxanes, their preparation and their use in cosmetic compounds
US4833225A (en) 1987-02-18 1989-05-23 Th. Goldschdidt AG Polyquaternary polysiloxane polymers, their synthesis and use in cosmetic preparations
US4891166A (en) 1987-06-06 1990-01-02 Th. Goldschmidt Ag Diquaternary polysiloxanes, their synthesis and use in cosmetic preparations
EP0339712A1 (en) 1988-04-28 1989-11-02 Berol Nobel AB Method for preparing flat or semi-flat water paints
EP0412705A2 (en) 1989-08-07 1991-02-13 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions
EP0415705A2 (en) 1989-08-28 1991-03-06 Minnesota Mining And Manufacturing Company Conformable polymeric marking sheet
US5344643A (en) 1990-12-21 1994-09-06 Dowbrands L.P. Shampoo-conditioning composition and method of making
EP0530974A1 (en) 1991-08-05 1993-03-10 Unilever Plc Hair care composition
EP0555155B1 (en) 1992-02-07 1996-07-24 L'oreal Cosmetic composition containing a surfactant such as an alkylpolyglycoside and/or polyglycerol and an urethanpolyether
US5478562A (en) 1992-02-07 1995-12-26 L'oreal Cosmetic composition containing at least one surface-active agent of the alkyl polyglycoside and/or polyglycerolated type and at least one polyetherurethane
EP0617607A1 (en) 1992-10-20 1994-10-05 Alberto Culver Co Hair care composition containing dispersed silicone oil.
US5294692A (en) 1993-06-30 1994-03-15 National Starch And Chemical Investment Holding Corporation Associative monomers and polymers
EP0637600A1 (en) 1993-08-04 1995-02-08 L'oreal New polyester polyurethanes, their preparation process, pseudo-latex prepared from these polyester polyurethanes and their use in cosmetic compositions
EP0648485A1 (en) 1993-10-15 1995-04-19 L'oreal Aqueous nail varnish containing dispersed particles of anionic polyester-polyurethane
US5538717A (en) 1993-10-15 1996-07-23 L'oreal Aqueous nail polish containing as film-forming substance particles of polyester-polyurethane which are anionic in dispersion
US5661118A (en) 1994-04-22 1997-08-26 L'oreal Hair and skin washing and treatment compositions based on ceramide and/or glycoceramide and on polymers containing cationic groups
DE4438846A1 (en) 1994-11-02 1996-05-09 Henkel Kgaa Hair treatment products
EP0714654A1 (en) 1994-12-03 1996-06-05 Wella Aktiengesellschaft Composition and process for permanent waving of hair
FR2733910A1 (en) 1995-05-12 1996-11-15 Oreal COMPOSITION IN THE FORM OF AEROSOL FOAM BASED ON POLYURETHANE AND ANIONIC POLYMER
EP0745373A1 (en) 1995-05-12 1996-12-04 L'oreal Aerosol foam composition based on polyurethane and an anionic polymer
FR2738835A1 (en) 1995-09-18 1997-03-21 Oreal THICKNESS COMPOSITION IN AQUEOUS MEDIUM, PROCESS FOR THICKENING OF AN AQUEOUS MEDIUM AND USES IN COSMETICS
FR2750047A1 (en) 1996-06-19 1997-12-26 Oreal Cosmetic or dermatological composition in form of viscous aqueous gel for topical application in hair dressing and styling gels
EP0824914A1 (en) 1996-08-16 1998-02-25 National Starch and Chemical Investment Holding Corporation Thickened personal care composition
FR2758262A1 (en) 1997-01-14 1998-07-17 Oreal COSMETIC OR DERMATOLOGICAL COMPOSITION IN THE FORM OF A GEL CONTAINING A MIXTURE OF AN ASSOCIATIVE COPOLYMER, A SURFACTANT AND AN INSOLUBLE PACKAGING AGENT

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
English language Derwent Abstract of DE 37 05 121. 9/88.
English language Derwent Abstract of DE 44 38 846. 10/88.
English language Derwent Abstract of EP 0 637 600. 2/95.
English language Derwent Abstract of EP 0 714 654. 6/96.
English language Derwent Abstract of EP 0 745 373. 12/96.
English language Derwent Abstract of FR 2 733 910. 11/96.
English language Derwent Abstract of FR 2 738 835. 3/97.
English language Derwent Abstract of FR 2 750 047. 12/97.
English language Derwent Abstract of FR 2 758 262. 7/98.

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030129210A1 (en) * 2002-01-09 2003-07-10 Economy Mud Products Company Uses of flaked cationic potato starch
US20050129639A1 (en) * 2003-11-07 2005-06-16 Eric Quemin Makeup composition comprising an emulsion
US20060184147A1 (en) * 2005-02-16 2006-08-17 Hamed Othman A Treatment composition for making acquisition fluff pulp in sheet form
WO2006088995A2 (en) * 2005-02-16 2006-08-24 Rayioner Trs Holdings Inc. Treatment composition for making acquisition fluff pulp in sheet form
WO2006088995A3 (en) * 2005-02-16 2007-01-04 Rayioner Trs Holdings Inc Treatment composition for making acquisition fluff pulp in sheet form
US7312297B2 (en) * 2005-02-16 2007-12-25 Rayonier Trs Holdings, Inc. Treatment composition for making acquisition fluff pulp in sheet form
US20080312397A1 (en) * 2007-06-14 2008-12-18 Bausch & Lomb Incorporated Silicone-Containing Prepolymers
US7691917B2 (en) * 2007-06-14 2010-04-06 Bausch & Lomb Incorporated Silcone-containing prepolymers
US20100256244A1 (en) * 2009-04-03 2010-10-07 Kroff Chemical Company Demulsification Compositions, Systems and Methods for Demulsifying and Separating Aqueous Emulsions
US8268975B2 (en) 2009-04-03 2012-09-18 Dow Agrosciences Llc Demulsification compositions, systems and methods for demulsifying and separating aqueous emulsions
US8796433B2 (en) 2009-04-03 2014-08-05 Kroff Chemical Company Demulsification compositions, systems and methods for demulsifying and separating aqueous emulsions
US9308474B2 (en) 2009-04-03 2016-04-12 Kroff Chemical Company Demulsification compositions, systems and methods for demulsifying and separating aqueous emulsions
US20120168664A1 (en) * 2009-09-15 2012-07-05 Evonik Goldschmidt Gmbh Novel polysiloxanes having quaternary ammonium groups and use thereof
US8916511B2 (en) * 2009-09-15 2014-12-23 Evonik Degussa Gmbh Polysiloxanes having quaternary ammonium groups and use thereof
EP2335680A1 (en) * 2009-12-18 2011-06-22 KPSS-Kao Professional Salon Services GmbH Cleansing composition
WO2011072855A1 (en) * 2009-12-18 2011-06-23 Kpss-Kao Professional Salon Services Gmbh Cleansing composition

Also Published As

Publication number Publication date
JP3930060B2 (en) 2007-06-13
ATE222086T1 (en) 2002-08-15
DK0975315T3 (en) 2002-12-09
FR2774902B1 (en) 2002-07-19
PT975315E (en) 2002-12-31
AU1882999A (en) 1999-08-30
ES2182389T3 (en) 2003-03-01
CN1259035A (en) 2000-07-05
WO1999040892A1 (en) 1999-08-19
FR2774902A1 (en) 1999-08-20
BR9807939A (en) 2000-02-22
EP0975315A1 (en) 2000-02-02
DE69807205D1 (en) 2002-09-19
CA2285684A1 (en) 1999-08-19
JP2000510495A (en) 2000-08-15
CA2285684C (en) 2006-05-16
EP0975315B1 (en) 2002-08-14
DE69807205T2 (en) 2003-02-06

Similar Documents

Publication Publication Date Title
CN103607994B (en) Composition and its cosmetic use comprising alkoxy silane and modified starch
EP0532256B1 (en) Method of preparing amine functional silicone microemulsions
CN101117385B (en) New polysiloxanes with quaternary ammonium groups, method for their manufacture and their use in cleaning and treating formulations
US6613315B1 (en) Cosmetic composition comprising at least one nonionic amphiphilic associative polyurethane and at least one nonionic polymer with fatty chains
KR0164212B1 (en) Vehicle systems for use in cosmetic compositions
EP0412706B1 (en) Vehicle systems for use in cosmetic compostions
US5019377A (en) Low glass transistion temperature adhesive copolymers for use in hair styling products
HUT66183A (en) Multicomponent hair care compositions having -among others- plasticizing effect
KR101632609B1 (en) Aminofunctional endblocked silicone polyether copolymers in personal care compositions
GB2144329A (en) Compositions and process for treating hair
US6258367B1 (en) Cosmetic composition comprising at least one nonionic amphiphilic associative polyurethane and at least one quaternary silicone
EP0320218A2 (en) Low glass transition temperature adhesive copolymers for use in hair styling products
KR20080031205A (en) Personal care compositions comprising saccharide-siloxane copolymers
PT100267A (en) COSMETIC COMPOSITIONS CONTAINING NON-IONIC POLYMER HYDROFOBICALLY AND AMNON SURFACTANT QUATERNARY INSATURADO
CN1377250A (en) Compositions for care of hair
JP5639040B2 (en) Method and composition for improving hair color retention
JP6585736B2 (en) Method for forming a styling hair care composition
EP0340269A1 (en) Conditioning compositions
US11666521B2 (en) Conditioning compositions containing cationic compounds, a silane compound and silica particles and methods for use
JP3761440B2 (en) Hair cosmetics
JP6765922B2 (en) Emulsion composition for hair cosmetics
JP2722243B2 (en) Hair cosmetics
JP3270776B2 (en) Hair cosmetics
JP2000086436A (en) Silicone emulsion composition and cosmetic prepared by using the same
JPH05507471A (en) Clean conditioning composition for hair

Legal Events

Date Code Title Description
AS Assignment

Owner name: L'OREAL S.A., FRANCE

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:DUPUIS, CHRISTINE;REEL/FRAME:010595/0330

Effective date: 19991027

FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

CC Certificate of correction
FPAY Fee payment

Year of fee payment: 4

REMI Maintenance fee reminder mailed
LAPS Lapse for failure to pay maintenance fees
STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362

FP Lapsed due to failure to pay maintenance fee

Effective date: 20090710